Question

Question: The following two-step procedure was used to prepare a sulfide from a diol. Draw theintermediate formed in Reaction [1] and draw a mechanism for Reaction [2].

Short answer

Answer

The intermediate formed in reaction [1]

The mechanism of reaction [2]

Step-by-step solution

Step-by-Step Solution Step 1: Function of mesyl chloride

Mesyl chloride $\left({\mathrm{CH}}_3{\mathrm{SO}}_2\mathrm{Cl}\right)$converts alcohol to a good leaving -OMs group.

Addition of mesyl chloride to the alcohol group

Mechanism for formation of product

Once the alcohol is converted to the god leaving -OMs group, sodium sulfide can react with any of the two -OMs group. The sulfur then attacks the carbon center of the other -OMs group and leads to the formation of the given product.

${\mathrm{S}}_{\mathrm{N}}2$ attack of sulfur at the electrophilic carbon center